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Alan was raised in Evansville, Indiana, where he graduated from Reitz High School in 1996. He went on to a degree from Western Kentucky University in 2000. His parents are Karen and Larry Gerbig.
Alan's early work includes the Bud Light beer television commercial "The Lucky Chair", with Stevie Wonder, that premiered during the 2013 Super Bowl. As Matthew Gerbig, he appeared in the films Charlie's War (2003) and Bell Witch Haunting (2004) before taking his stage name. Alan's work includes a recurring role in 2007 on the CBS streaming series Ghost Whisperer: The Other Side, a companion to the network series Ghost Whisperer, and in 2017 and 2018 on the Netflix series 13 Reasons Why; and the recurring role of Chris Merrill in the Hulu series Castle Rock.
A 2009 Folger's coffee commercial with actress Catherine Combs, which became a Christmastime staple for several years, developed a fan following over what some perceived as romantic undertones between siblings, inspiring comedy sketches from Daniel Tosh and Chelsea Handler.
Alan is in a relationship with English actress Camilla Luddington. The couple welcomed their daughter Hayden born on March 9, 2017. Alan proposed to Luddington on December 31, 2017. The couple married on August 17, 2019. The couple welcomed their son Lucas born on August 7, 2020.